1-Methyl-3-phenyl-1H-1,2,4-triazole-5-carbaldehyde → (3,3-dimethyl-1,3-dihydroisobenzofuran-5-yl)(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

BuLi (0.36 mL, 1.6 M in hexanes, 0.57 mmol) was added dropwise to a solution of Intermediate 388.2 (110 mg, 0.49 mmol) in THF (5 mL) at −78° C. After stirring 5 min, a solution of Intermediate 386.1 (100 mg, 0.54 mmol) in THF (3 mL) was added. The mixture was warmed to 0° C. over 2 h and quenched with sat. NH4Cl (1 mL). The mixture was diluted with H2O (20 mL) and extracted with EtOAc (3×20 mL). The organics were combined, washed with brine, dried (Na2SO4) and concentrated. Purification by flash chromatography (hexanes, EtOAc) yielded 63 mg of Intermediate 388.3 as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.37 (s, 6 H) 3.48 (s, 3H) 4.90 (s, 2H) 5.68 (s, 1H) 6.01 (s, 1H) 6.93-7.00 (m, 1H) 7.10-7.14 (m, 1H) 7.14-7.19 (m, 1H) 7.28-7.38 (m, 3H) 7.89-7.95 (m, 2H)

Provenance & Evidence